Issue 40, 2020

Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride

Abstract

We report a mild method for the selective deprotection of the N-Boc group from a structurally diverse set of compounds, encompassing aliphatic, aromatic, and heterocyclic substrates by using oxalyl chloride in methanol. The reactions take place under room temperature conditions for 1–4 h with yields up to 90%. This mild procedure was applied to a hybrid, medicinally active compound FC1, which is a novel dual inhibitor of IDO1 and DNA Pol gamma. A broader mechanism involving the electrophilic character of oxalyl chloride is postulated for this deprotection strategy.

Graphical abstract: Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
07 May 2020
Accepted
12 Jun 2020
First published
23 Jun 2020
This article is Open Access
Creative Commons BY license

RSC Adv., 2020,10, 24017-24026

Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride

N. George, S. Ofori, S. Parkin and S. G. Awuah, RSC Adv., 2020, 10, 24017 DOI: 10.1039/D0RA04110F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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